Water → HCID 44223427, compound

HRID 1943904Notes

Reaction equation

HRID 1943904 reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[C:7]([F:18])[C:3]=1[C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.[N:41]1([C:46]2[C:54]3[C:49](=[N:50][CH:51]=[C:52]([NH2:55])[CH:53]=3)[NH:48][N:47]=2)[CH:45]=[CH:44][N:43]=[CH:42]1>CN(C=O)C>[N:41]1([C:46]2[C:54]3[C:49](=[N:50][CH:51]=[C:52]([NH:55][C:4](=[O:6])[C:3]4[C:7]([F:18])=[CH:8][CH:9]=[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:2]=4[F:1])[CH:53]=3)[NH:48][N:47]=2)[CH:45]=[CH:44][N:43]=[CH:42]1

Participants

7

Reactant 5

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 67088915HCID 67088915, compound

Product 1

HCID 44223427HCID 44223427, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Difluoro-3-(propylsulfonamido)benzoic acid (140 mg, 0.495 mmol), HOBt.H2O (89 mg, 0.584 mmol), and EDCI (120 mg, 0.674 mmol) was added to 3-(1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-5-amine (90 mg, 0.450 mmol) in DMF (10 mL). The mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated, and the residue partitioned between ethyl acetate and water. The ethyl acetate was washed with brine, dried over magnesium sulfate, filtered, and concentrated to an oil. The crude product was purified by column chromatography (10:1 DCM:MeOH), which was followed by trituration with DCM to afford N-(3-(1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (57.7 mg, 28% yield) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.80 (d, 1H), 8.74 (d, 1H), 8.36 (s, 1H), 7.80 (s, 1H), 7.70-7.64 (m, 1H), 7.27 (s, 1H), 7.17-7.12 (m, 1H), 3.14-3.09 (m, 2H), 1.92-1.82 (m, 2H), 1.06 (t, 3H); m/z (ESI-pos) M+1 462.2.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe crude product was purified by column chromatography (10:1 DCM:MeOH), which

Sources & evidence

ORD record
ord-231f2914329649a18af29e30e4d8750c
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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